S3E15: Can This Jack Be Happy with a Jill That’s His Equal?
52-yr-old Jack has been single for the past 25 years and only dated much younger women. 46-yr-old Charleigh is worried that this makes Jack see her as more of an “age-appropriate companion” rather than a girlfriend. Adding to Charleigh’s anxiety is the fact that she was cheated on by her ex-husband when he was away on business, and Jack is a bit of a big-spending partier when he’s out-of-town. Charleigh wants to know if Jack can really see her as his “one” despite friends saying Jack is the happiest they’ve ever seen him.